(2R,4S,5S)-5-[[(4R)-3-(tert-butyloxycarbonyl)-2,2-dimethylthiazolidine-4-carbonyl]amino]-4-[(tert-butyldimethylsilyl)oxy]-2-(phenylmethyl)heptanoic acid

Base Information

• Chemical Name: (2R,4S,5S)-5-[[(4R)-3-(tert-butyloxycarbonyl)-2,2-dimethylthiazolidine-4-carbonyl]amino]-4-[(tert-butyldimethylsilyl)oxy]-2-(phenylmethyl)heptanoic acid
• CAS No.: 331821-54-6
• Molecular Formula: C₃₁H₅₂N₂O₆SSi
• Molecular Weight: 608.915

Synonyms:(2R,4S,5S)-5-[[(4R)-3-(tert-butyloxycarbonyl)-2,2-dimethylthiazolidine-4-carbonyl]amino]-4-[(tert-butyldimethylsilyl)oxy]-2-(phenylmethyl)heptanoic acid

Chemical Property of (2R,4S,5S)-5-[[(4R)-3-(tert-butyloxycarbonyl)-2,2-dimethylthiazolidine-4-carbonyl]amino]-4-[(tert-butyldimethylsilyl)oxy]-2-(phenylmethyl)heptanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4S,5S)-5-[[(4R)-3-(tert-butyloxycarbonyl)-2,2-dimethylthiazolidine-4-carbonyl]amino]-4-[(tert-butyldimethylsilyl)oxy]-2-(phenylmethyl)heptanoic acid

There total 8 articles about (2R,4S,5S)-5-[[(4R)-3-(tert-butyloxycarbonyl)-2,2-dimethylthiazolidine-4-carbonyl]amino]-4-[(tert-butyldimethylsilyl)oxy]-2-(phenylmethyl)heptanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 73.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (R)-4-((1S,2S,4R)-4-Carboxy-1-ethyl-2-hydroxy-5-phenyl-pentylcarbamoyl)-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester → (2R,4S,5S)-5-[[(4R)-3-(tert-butyloxycarbonyl)-2,2-dimethylthiazolidine-4-carbonyl]amino]-4-[(tert-butyldimethylsilyl)oxy]-2-(phenylmethyl)heptanoic acid (331821-54-6)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1021/jo001257i

Reference yield:

(E)-1-bromo-2-pentene (7348-71-2) → (2R,4S,5S)-5-[[(4R)-3-(tert-butyloxycarbonyl)-2,2-dimethylthiazolidine-4-carbonyl]amino]-4-[(tert-butyldimethylsilyl)oxy]-2-(phenylmethyl)heptanoic acid (331821-54-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-BuLi; diisopropylamine; LiCl / hexane; tetrahydrofuran / 1.33 h / -78 - 20 °C

1.2: 93 percent / tetrahydrofuran; hexane / 2 h / 0 °C

2.1: N-bromosuccinimide; glacial acetic acid / tetrahydrofuran; H₂O / 4 h / Heating

3.1: 70 percent / sodium azide / dimethylformamide / 50 °C

4.1: H₂ / Pd/C / methanol / 4 h / 760.05 Torr

5.1: 81 percent / diisopropylethylamine / tetrahydrofuran / 20 °C

6.1: NaOH / dioxane; H₂O / 2 h / 20 °C

7.1: 73 percent / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; sodium hydroxide; N-Bromosuccinimide; n-butyllithium; sodium azide; hydrogen; acetic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo001257i

Reference yield:

N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-3-phenylpropanamide (14980-86-0,42407-58-9) → (2R,4S,5S)-5-[[(4R)-3-(tert-butyloxycarbonyl)-2,2-dimethylthiazolidine-4-carbonyl]amino]-4-[(tert-butyldimethylsilyl)oxy]-2-(phenylmethyl)heptanoic acid (331821-54-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: n-BuLi; diisopropylamine; LiCl / hexane; tetrahydrofuran / 1.33 h / -78 - 20 °C

1.2: 93 percent / tetrahydrofuran; hexane / 2 h / 0 °C

2.1: N-bromosuccinimide; glacial acetic acid / tetrahydrofuran; H₂O / 4 h / Heating

3.1: 70 percent / sodium azide / dimethylformamide / 50 °C

4.1: H₂ / Pd/C / methanol / 4 h / 760.05 Torr

5.1: 81 percent / diisopropylethylamine / tetrahydrofuran / 20 °C

6.1: NaOH / dioxane; H₂O / 2 h / 20 °C

7.1: 73 percent / imidazole / dimethylformamide / 20 °C

With 1H-imidazole; sodium hydroxide; N-Bromosuccinimide; n-butyllithium; sodium azide; hydrogen; acetic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; lithium chloride; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo001257i

upstream raw materials:

tert-butyldimethylsilyl chloride

(E)-1-bromo-2-pentene

N-((1S,2S)-1-hydroxy-1-phenylpropan-2-yl)-N-methyl-3-phenylpropanamide

(1'R,3R,5S)-3-benzyl-5-(1'-bromopropyl)dihydrofuran-2-one

Downstream raw materials:

(R)-4-[(1S,2S,4R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-ethyl-4-((S)-1-methoxycarbonyl-3-methylsulfanyl-propylcarbamoyl)-5-phenyl-pentylcarbamoyl]-2,2-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester

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